JP4951909B2 - Pigment composition and ink - Google Patents
Pigment composition and ink Download PDFInfo
- Publication number
- JP4951909B2 JP4951909B2 JP2005273776A JP2005273776A JP4951909B2 JP 4951909 B2 JP4951909 B2 JP 4951909B2 JP 2005273776 A JP2005273776 A JP 2005273776A JP 2005273776 A JP2005273776 A JP 2005273776A JP 4951909 B2 JP4951909 B2 JP 4951909B2
- Authority
- JP
- Japan
- Prior art keywords
- pigment
- group
- parts
- alkali
- soluble resin
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
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- 239000000049 pigment Substances 0.000 title claims description 118
- 239000000203 mixture Substances 0.000 title claims description 52
- 239000011347 resin Substances 0.000 claims description 56
- 229920005989 resin Polymers 0.000 claims description 56
- 239000002253 acid Substances 0.000 claims description 19
- 125000003277 amino group Chemical group 0.000 claims description 19
- 230000002378 acidificating effect Effects 0.000 claims description 18
- 239000000178 monomer Substances 0.000 claims description 18
- 125000000524 functional group Chemical group 0.000 claims description 17
- 150000003242 quaternary ammonium salts Chemical class 0.000 claims description 15
- 239000003960 organic solvent Substances 0.000 claims description 10
- 239000006229 carbon black Substances 0.000 claims description 9
- 125000000217 alkyl group Chemical group 0.000 claims description 8
- 125000004432 carbon atom Chemical group C* 0.000 claims description 8
- NRCMAYZCPIVABH-UHFFFAOYSA-N Quinacridone Chemical compound N1C2=CC=CC=C2C(=O)C2=C1C=C1C(=O)C3=CC=CC=C3NC1=C2 NRCMAYZCPIVABH-UHFFFAOYSA-N 0.000 claims description 6
- 125000000751 azo group Chemical group [*]N=N[*] 0.000 claims description 6
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 6
- 125000001453 quaternary ammonium group Chemical group 0.000 claims description 5
- 125000004103 aminoalkyl group Chemical group 0.000 claims description 4
- PYKYMHQGRFAEBM-UHFFFAOYSA-N anthraquinone Natural products CCC(=O)c1c(O)c2C(=O)C3C(C=CC=C3O)C(=O)c2cc1CC(=O)OC PYKYMHQGRFAEBM-UHFFFAOYSA-N 0.000 claims description 4
- 150000004056 anthraquinones Chemical class 0.000 claims description 4
- MYONAGGJKCJOBT-UHFFFAOYSA-N benzimidazol-2-one Chemical compound C1=CC=CC2=NC(=O)N=C21 MYONAGGJKCJOBT-UHFFFAOYSA-N 0.000 claims description 4
- 125000002843 carboxylic acid group Chemical group 0.000 claims description 4
- PPSZHCXTGRHULJ-UHFFFAOYSA-N dioxazine Chemical compound O1ON=CC=C1 PPSZHCXTGRHULJ-UHFFFAOYSA-N 0.000 claims description 4
- PXZQEOJJUGGUIB-UHFFFAOYSA-N isoindolin-1-one Chemical compound C1=CC=C2C(=O)NCC2=C1 PXZQEOJJUGGUIB-UHFFFAOYSA-N 0.000 claims description 4
- GWVMLCQWXVFZCN-UHFFFAOYSA-N isoindoline Chemical compound C1=CC=C2CNCC2=C1 GWVMLCQWXVFZCN-UHFFFAOYSA-N 0.000 claims description 4
- DGBWPZSGHAXYGK-UHFFFAOYSA-N perinone Chemical compound C12=NC3=CC=CC=C3N2C(=O)C2=CC=C3C4=C2C1=CC=C4C(=O)N1C2=CC=CC=C2N=C13 DGBWPZSGHAXYGK-UHFFFAOYSA-N 0.000 claims description 4
- 125000002080 perylenyl group Chemical group C1(=CC=C2C=CC=C3C4=CC=CC5=CC=CC(C1=C23)=C45)* 0.000 claims description 4
- CSHWQDPOILHKBI-UHFFFAOYSA-N peryrene Natural products C1=CC(C2=CC=CC=3C2=C2C=CC=3)=C3C2=CC=CC3=C1 CSHWQDPOILHKBI-UHFFFAOYSA-N 0.000 claims description 4
- IEQIEDJGQAUEQZ-UHFFFAOYSA-N phthalocyanine Chemical compound N1C(N=C2C3=CC=CC=C3C(N=C3C4=CC=CC=C4C(=N4)N3)=N2)=C(C=CC=C2)C2=C1N=C1C2=CC=CC=C2C4=N1 IEQIEDJGQAUEQZ-UHFFFAOYSA-N 0.000 claims description 4
- LLBIOIRWAYBCKK-UHFFFAOYSA-N pyranthrene-8,16-dione Chemical compound C12=CC=CC=C2C(=O)C2=CC=C3C=C4C5=CC=CC=C5C(=O)C5=C4C4=C3C2=C1C=C4C=C5 LLBIOIRWAYBCKK-UHFFFAOYSA-N 0.000 claims description 4
- FYNROBRQIVCIQF-UHFFFAOYSA-N pyrrolo[3,2-b]pyrrole-5,6-dione Chemical compound C1=CN=C2C(=O)C(=O)N=C21 FYNROBRQIVCIQF-UHFFFAOYSA-N 0.000 claims description 4
- 125000000542 sulfonic acid group Chemical group 0.000 claims description 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 3
- IZMJMCDDWKSTTK-UHFFFAOYSA-N quinoline yellow Chemical compound C1=CC=CC2=NC(C3C(C4=CC=CC=C4C3=O)=O)=CC=C21 IZMJMCDDWKSTTK-UHFFFAOYSA-N 0.000 claims description 3
- 229920001577 copolymer Polymers 0.000 claims description 2
- 150000003863 ammonium salts Chemical class 0.000 claims 1
- 125000003262 carboxylic acid ester group Chemical group [H]C([H])([*:2])OC(=O)C([H])([H])[*:1] 0.000 claims 1
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 40
- 239000006185 dispersion Substances 0.000 description 32
- OZAIFHULBGXAKX-UHFFFAOYSA-N 2-(2-cyanopropan-2-yldiazenyl)-2-methylpropanenitrile Chemical compound N#CC(C)(C)N=NC(C)(C)C#N OZAIFHULBGXAKX-UHFFFAOYSA-N 0.000 description 21
- -1 viridian Chemical compound 0.000 description 16
- CCTFMNIEFHGTDU-UHFFFAOYSA-N 3-methoxypropyl acetate Chemical compound COCCCOC(C)=O CCTFMNIEFHGTDU-UHFFFAOYSA-N 0.000 description 15
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 15
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 14
- 230000000052 comparative effect Effects 0.000 description 12
- 229910052757 nitrogen Inorganic materials 0.000 description 12
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 11
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 11
- 238000006243 chemical reaction Methods 0.000 description 11
- 230000000694 effects Effects 0.000 description 11
- 238000000034 method Methods 0.000 description 11
- 238000004519 manufacturing process Methods 0.000 description 10
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 9
- 239000004576 sand Substances 0.000 description 9
- 238000003860 storage Methods 0.000 description 9
- 239000000243 solution Substances 0.000 description 8
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 7
- 239000002585 base Substances 0.000 description 7
- 238000001035 drying Methods 0.000 description 7
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 239000002270 dispersing agent Substances 0.000 description 6
- 239000002904 solvent Substances 0.000 description 6
- CERQOIWHTDAKMF-UHFFFAOYSA-M Methacrylate Chemical compound CC(=C)C([O-])=O CERQOIWHTDAKMF-UHFFFAOYSA-M 0.000 description 5
- VVQNEPGJFQJSBK-UHFFFAOYSA-N Methyl methacrylate Chemical compound COC(=O)C(C)=C VVQNEPGJFQJSBK-UHFFFAOYSA-N 0.000 description 5
- 238000004040 coloring Methods 0.000 description 5
- 229910001873 dinitrogen Inorganic materials 0.000 description 5
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 5
- 239000011259 mixed solution Substances 0.000 description 5
- 238000002156 mixing Methods 0.000 description 5
- 239000012860 organic pigment Substances 0.000 description 5
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 4
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- 238000000576 coating method Methods 0.000 description 4
- 239000007787 solid Substances 0.000 description 4
- KDYFGRWQOYBRFD-UHFFFAOYSA-N succinic acid Chemical compound OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 4
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 3
- 150000001412 amines Chemical class 0.000 description 3
- 150000001733 carboxylic acid esters Chemical group 0.000 description 3
- 239000011248 coating agent Substances 0.000 description 3
- 239000010941 cobalt Substances 0.000 description 3
- 229910017052 cobalt Inorganic materials 0.000 description 3
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 description 3
- 239000011521 glass Substances 0.000 description 3
- 238000005259 measurement Methods 0.000 description 3
- 239000002245 particle Substances 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- ZGEGCLOFRBLKSE-UHFFFAOYSA-N 1-Heptene Chemical compound CCCCCC=C ZGEGCLOFRBLKSE-UHFFFAOYSA-N 0.000 description 2
- LIKMAJRDDDTEIG-UHFFFAOYSA-N 1-hexene Chemical compound CCCCC=C LIKMAJRDDDTEIG-UHFFFAOYSA-N 0.000 description 2
- KWKAKUADMBZCLK-UHFFFAOYSA-N 1-octene Chemical compound CCCCCCC=C KWKAKUADMBZCLK-UHFFFAOYSA-N 0.000 description 2
- FPZWZCWUIYYYBU-UHFFFAOYSA-N 2-(2-ethoxyethoxy)ethyl acetate Chemical compound CCOCCOCCOC(C)=O FPZWZCWUIYYYBU-UHFFFAOYSA-N 0.000 description 2
- JKNCOURZONDCGV-UHFFFAOYSA-N 2-(dimethylamino)ethyl 2-methylprop-2-enoate Chemical compound CN(C)CCOC(=O)C(C)=C JKNCOURZONDCGV-UHFFFAOYSA-N 0.000 description 2
- AFABGHUZZDYHJO-UHFFFAOYSA-N 2-Methylpentane Chemical compound CCCC(C)C AFABGHUZZDYHJO-UHFFFAOYSA-N 0.000 description 2
- QQZOPKMRPOGIEB-UHFFFAOYSA-N 2-Oxohexane Chemical compound CCCCC(C)=O QQZOPKMRPOGIEB-UHFFFAOYSA-N 0.000 description 2
- NQBXSWAWVZHKBZ-UHFFFAOYSA-N 2-butoxyethyl acetate Chemical compound CCCCOCCOC(C)=O NQBXSWAWVZHKBZ-UHFFFAOYSA-N 0.000 description 2
- SYBYTAAJFKOIEJ-UHFFFAOYSA-N 3-Methylbutan-2-one Chemical compound CC(C)C(C)=O SYBYTAAJFKOIEJ-UHFFFAOYSA-N 0.000 description 2
- PFCHFHIRKBAQGU-UHFFFAOYSA-N 3-hexanone Chemical compound CCCC(=O)CC PFCHFHIRKBAQGU-UHFFFAOYSA-N 0.000 description 2
- HCFAJYNVAYBARA-UHFFFAOYSA-N 4-heptanone Chemical compound CCCC(=O)CCC HCFAJYNVAYBARA-UHFFFAOYSA-N 0.000 description 2
- FFWSICBKRCICMR-UHFFFAOYSA-N 5-methyl-2-hexanone Chemical compound CC(C)CCC(C)=O FFWSICBKRCICMR-UHFFFAOYSA-N 0.000 description 2
- MRABAEUHTLLEML-UHFFFAOYSA-N Butyl lactate Chemical compound CCCCOC(=O)C(C)O MRABAEUHTLLEML-UHFFFAOYSA-N 0.000 description 2
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- DXVYLFHTJZWTRF-UHFFFAOYSA-N Ethyl isobutyl ketone Chemical compound CCC(=O)CC(C)C DXVYLFHTJZWTRF-UHFFFAOYSA-N 0.000 description 2
- HYTRYEXINDDXJK-UHFFFAOYSA-N Ethyl isopropyl ketone Chemical compound CCC(=O)C(C)C HYTRYEXINDDXJK-UHFFFAOYSA-N 0.000 description 2
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 2
- UQSXHKLRYXJYBZ-UHFFFAOYSA-N Iron oxide Chemical compound [Fe]=O UQSXHKLRYXJYBZ-UHFFFAOYSA-N 0.000 description 2
- MPIAGWXWVAHQBB-UHFFFAOYSA-N [3-prop-2-enoyloxy-2-[[3-prop-2-enoyloxy-2,2-bis(prop-2-enoyloxymethyl)propoxy]methyl]-2-(prop-2-enoyloxymethyl)propyl] prop-2-enoate Chemical compound C=CC(=O)OCC(COC(=O)C=C)(COC(=O)C=C)COCC(COC(=O)C=C)(COC(=O)C=C)COC(=O)C=C MPIAGWXWVAHQBB-UHFFFAOYSA-N 0.000 description 2
- AUNAPVYQLLNFOI-UHFFFAOYSA-L [Pb++].[Pb++].[Pb++].[O-]S([O-])(=O)=O.[O-][Cr]([O-])(=O)=O.[O-][Mo]([O-])(=O)=O Chemical compound [Pb++].[Pb++].[Pb++].[O-]S([O-])(=O)=O.[O-][Cr]([O-])(=O)=O.[O-][Mo]([O-])(=O)=O AUNAPVYQLLNFOI-UHFFFAOYSA-L 0.000 description 2
- 239000000654 additive Substances 0.000 description 2
- 239000003513 alkali Substances 0.000 description 2
- 150000008064 anhydrides Chemical class 0.000 description 2
- TZCXTZWJZNENPQ-UHFFFAOYSA-L barium sulfate Chemical compound [Ba+2].[O-]S([O-])(=O)=O TZCXTZWJZNENPQ-UHFFFAOYSA-L 0.000 description 2
- 239000001191 butyl (2R)-2-hydroxypropanoate Substances 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- DMEGYFMYUHOHGS-UHFFFAOYSA-N cycloheptane Chemical compound C1CCCCCC1 DMEGYFMYUHOHGS-UHFFFAOYSA-N 0.000 description 2
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 2
- HGCIXCUEYOPUTN-UHFFFAOYSA-N cyclohexene Chemical compound C1CCC=CC1 HGCIXCUEYOPUTN-UHFFFAOYSA-N 0.000 description 2
- NNBZCPXTIHJBJL-UHFFFAOYSA-N decalin Chemical compound C1CCCC2CCCCC21 NNBZCPXTIHJBJL-UHFFFAOYSA-N 0.000 description 2
- SNRUBQQJIBEYMU-UHFFFAOYSA-N dodecane Chemical compound CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 description 2
- 235000019441 ethanol Nutrition 0.000 description 2
- XLLIQLLCWZCATF-UHFFFAOYSA-N ethylene glycol monomethyl ether acetate Natural products COCCOC(C)=O XLLIQLLCWZCATF-UHFFFAOYSA-N 0.000 description 2
- 238000010528 free radical solution polymerization reaction Methods 0.000 description 2
- CATSNJVOTSVZJV-UHFFFAOYSA-N heptan-2-one Chemical compound CCCCCC(C)=O CATSNJVOTSVZJV-UHFFFAOYSA-N 0.000 description 2
- NGAZZOYFWWSOGK-UHFFFAOYSA-N heptan-3-one Chemical compound CCCCC(=O)CC NGAZZOYFWWSOGK-UHFFFAOYSA-N 0.000 description 2
- AOGQPLXWSUTHQB-UHFFFAOYSA-N hexyl acetate Chemical compound CCCCCCOC(C)=O AOGQPLXWSUTHQB-UHFFFAOYSA-N 0.000 description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 2
- 239000001023 inorganic pigment Substances 0.000 description 2
- ZUBZATZOEPUUQF-UHFFFAOYSA-N isononane Chemical compound CCCCCCC(C)C ZUBZATZOEPUUQF-UHFFFAOYSA-N 0.000 description 2
- HJOVHMDZYOCNQW-UHFFFAOYSA-N isophorone Chemical compound CC1=CC(=O)CC(C)(C)C1 HJOVHMDZYOCNQW-UHFFFAOYSA-N 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 2
- BKIMMITUMNQMOS-UHFFFAOYSA-N nonane Chemical compound CCCCCCCCC BKIMMITUMNQMOS-UHFFFAOYSA-N 0.000 description 2
- YLYBTZIQSIBWLI-UHFFFAOYSA-N octyl acetate Chemical compound CCCCCCCCOC(C)=O YLYBTZIQSIBWLI-UHFFFAOYSA-N 0.000 description 2
- XNLICIUVMPYHGG-UHFFFAOYSA-N pentan-2-one Chemical compound CCCC(C)=O XNLICIUVMPYHGG-UHFFFAOYSA-N 0.000 description 2
- FDPIMTJIUBPUKL-UHFFFAOYSA-N pentan-3-one Chemical compound CCC(=O)CC FDPIMTJIUBPUKL-UHFFFAOYSA-N 0.000 description 2
- 229920000642 polymer Polymers 0.000 description 2
- 239000003505 polymerization initiator Substances 0.000 description 2
- 238000006116 polymerization reaction Methods 0.000 description 2
- 150000003141 primary amines Chemical class 0.000 description 2
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 2
- 229930195734 saturated hydrocarbon Natural products 0.000 description 2
- 239000000377 silicon dioxide Substances 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 125000001424 substituent group Chemical group 0.000 description 2
- 239000001384 succinic acid Substances 0.000 description 2
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 2
- 229930195735 unsaturated hydrocarbon Natural products 0.000 description 2
- JTQQDDNCCLCMER-CLFAGFIQSA-N (z)-n-[(z)-octadec-9-enyl]octadec-9-en-1-amine Chemical compound CCCCCCCC\C=C/CCCCCCCCNCCCCCCCC\C=C/CCCCCCCC JTQQDDNCCLCMER-CLFAGFIQSA-N 0.000 description 1
- WBYWAXJHAXSJNI-VOTSOKGWSA-M .beta-Phenylacrylic acid Natural products [O-]C(=O)\C=C\C1=CC=CC=C1 WBYWAXJHAXSJNI-VOTSOKGWSA-M 0.000 description 1
- LZDKZFUFMNSQCJ-UHFFFAOYSA-N 1,2-diethoxyethane Chemical compound CCOCCOCC LZDKZFUFMNSQCJ-UHFFFAOYSA-N 0.000 description 1
- WGYZMNBUZFHYRX-UHFFFAOYSA-N 1-(1-methoxypropan-2-yloxy)propan-2-ol Chemical compound COCC(C)OCC(C)O WGYZMNBUZFHYRX-UHFFFAOYSA-N 0.000 description 1
- QWOZZTWBWQMEPD-UHFFFAOYSA-N 1-(2-ethoxypropoxy)propan-2-ol Chemical compound CCOC(C)COCC(C)O QWOZZTWBWQMEPD-UHFFFAOYSA-N 0.000 description 1
- WQHNZXURJISVCT-UHFFFAOYSA-N 1-butoxyethane-1,2-diol Chemical compound CCCCOC(O)CO WQHNZXURJISVCT-UHFFFAOYSA-N 0.000 description 1
- RWNUSVWFHDHRCJ-UHFFFAOYSA-N 1-butoxypropan-2-ol Chemical compound CCCCOCC(C)O RWNUSVWFHDHRCJ-UHFFFAOYSA-N 0.000 description 1
- FUWDFGKRNIDKAE-UHFFFAOYSA-N 1-butoxypropan-2-yl acetate Chemical compound CCCCOCC(C)OC(C)=O FUWDFGKRNIDKAE-UHFFFAOYSA-N 0.000 description 1
- RRQYJINTUHWNHW-UHFFFAOYSA-N 1-ethoxy-2-(2-ethoxyethoxy)ethane Chemical compound CCOCCOCCOCC RRQYJINTUHWNHW-UHFFFAOYSA-N 0.000 description 1
- JOLQKTGDSGKSKJ-UHFFFAOYSA-N 1-ethoxypropan-2-ol Chemical compound CCOCC(C)O JOLQKTGDSGKSKJ-UHFFFAOYSA-N 0.000 description 1
- LIPRQQHINVWJCH-UHFFFAOYSA-N 1-ethoxypropan-2-yl acetate Chemical compound CCOCC(C)OC(C)=O LIPRQQHINVWJCH-UHFFFAOYSA-N 0.000 description 1
- ARXJGSRGQADJSQ-UHFFFAOYSA-N 1-methoxypropan-2-ol Chemical compound COCC(C)O ARXJGSRGQADJSQ-UHFFFAOYSA-N 0.000 description 1
- OEYNWAWWSZUGDU-UHFFFAOYSA-N 1-methoxypropane-1,2-diol Chemical compound COC(O)C(C)O OEYNWAWWSZUGDU-UHFFFAOYSA-N 0.000 description 1
- JOERQAIRIDZWHX-UHFFFAOYSA-N 1-propoxy-2-(2-propoxypropoxy)propane Chemical compound CCCOCC(C)OCC(C)OCCC JOERQAIRIDZWHX-UHFFFAOYSA-N 0.000 description 1
- VXQBJTKSVGFQOL-UHFFFAOYSA-N 2-(2-butoxyethoxy)ethyl acetate Chemical compound CCCCOCCOCCOC(C)=O VXQBJTKSVGFQOL-UHFFFAOYSA-N 0.000 description 1
- YHYCMHWTYHPIQS-UHFFFAOYSA-N 2-(2-hydroxyethoxy)-1-methoxyethanol Chemical compound COC(O)COCCO YHYCMHWTYHPIQS-UHFFFAOYSA-N 0.000 description 1
- SBASXUCJHJRPEV-UHFFFAOYSA-N 2-(2-methoxyethoxy)ethanol Chemical compound COCCOCCO SBASXUCJHJRPEV-UHFFFAOYSA-N 0.000 description 1
- BJINVQNEBGOMCR-UHFFFAOYSA-N 2-(2-methoxyethoxy)ethyl acetate Chemical compound COCCOCCOC(C)=O BJINVQNEBGOMCR-UHFFFAOYSA-N 0.000 description 1
- JAHNSTQSQJOJLO-UHFFFAOYSA-N 2-(3-fluorophenyl)-1h-imidazole Chemical compound FC1=CC=CC(C=2NC=CN=2)=C1 JAHNSTQSQJOJLO-UHFFFAOYSA-N 0.000 description 1
- SJIXRGNQPBQWMK-UHFFFAOYSA-N 2-(diethylamino)ethyl 2-methylprop-2-enoate Chemical compound CCN(CC)CCOC(=O)C(C)=C SJIXRGNQPBQWMK-UHFFFAOYSA-N 0.000 description 1
- PTTPXKJBFFKCEK-UHFFFAOYSA-N 2-Methyl-4-heptanone Chemical compound CC(C)CC(=O)CC(C)C PTTPXKJBFFKCEK-UHFFFAOYSA-N 0.000 description 1
- WAEVWDZKMBQDEJ-UHFFFAOYSA-N 2-[2-(2-methoxypropoxy)propoxy]propan-1-ol Chemical compound COC(C)COC(C)COC(C)CO WAEVWDZKMBQDEJ-UHFFFAOYSA-N 0.000 description 1
- 125000000022 2-aminoethyl group Chemical group [H]C([*])([H])C([H])([H])N([H])[H] 0.000 description 1
- POAOYUHQDCAZBD-UHFFFAOYSA-N 2-butoxyethanol Chemical compound CCCCOCCO POAOYUHQDCAZBD-UHFFFAOYSA-N 0.000 description 1
- SZTBMYHIYNGYIA-UHFFFAOYSA-N 2-chloroacrylic acid Chemical compound OC(=O)C(Cl)=C SZTBMYHIYNGYIA-UHFFFAOYSA-N 0.000 description 1
- SVONRAPFKPVNKG-UHFFFAOYSA-N 2-ethoxyethyl acetate Chemical compound CCOCCOC(C)=O SVONRAPFKPVNKG-UHFFFAOYSA-N 0.000 description 1
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- UPGSWASWQBLSKZ-UHFFFAOYSA-N 2-hexoxyethanol Chemical compound CCCCCCOCCO UPGSWASWQBLSKZ-UHFFFAOYSA-N 0.000 description 1
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- GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 description 1
- 239000002966 varnish Substances 0.000 description 1
- PXXNTAGJWPJAGM-UHFFFAOYSA-N vertaline Natural products C1C2C=3C=C(OC)C(OC)=CC=3OC(C=C3)=CC=C3CCC(=O)OC1CC1N2CCCC1 PXXNTAGJWPJAGM-UHFFFAOYSA-N 0.000 description 1
- 239000004034 viscosity adjusting agent Substances 0.000 description 1
- 239000001993 wax Substances 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
- 239000001052 yellow pigment Substances 0.000 description 1
- 239000011787 zinc oxide Substances 0.000 description 1
- 235000014692 zinc oxide Nutrition 0.000 description 1
- 229910052984 zinc sulfide Inorganic materials 0.000 description 1
- DRDVZXDWVBGGMH-UHFFFAOYSA-N zinc;sulfide Chemical compound [S-2].[Zn+2] DRDVZXDWVBGGMH-UHFFFAOYSA-N 0.000 description 1
Landscapes
- Pigments, Carbon Blacks, Or Wood Stains (AREA)
- Inks, Pencil-Leads, Or Crayons (AREA)
Description
本発明は、分散性、流動性、保存安定性、乾燥再溶解性、基材密着性に優れたインキ等を与えうる顔料組成物に関する。 The present invention relates to a pigment composition that can provide an ink having excellent dispersibility, fluidity, storage stability, dry re-dissolvability, and substrate adhesion.
一般に、高濃度の顔料を安定して分散させることは難しく、製造工程やインキ製品等において種々の問題を引き起こすことが知られている。
例えば、微細粒子からなる顔料を含む分散体は往々にして高粘度を示すため、分散工程後における分散機からの製品の取り出しや輸送が困難なだけでなく、保管中にゲル化を起こし使用困難になる場合がある。さらに展色物に関しては光沢の低下、レベリング不良等、表面状態が不良になるおそれがある。
また、異種の顔料を混合して使用する場合、凝集による色別れや、沈降などの現象により展色物に色むらや著しく着色力が低下する場合がある。
In general, it is difficult to stably disperse a high concentration of pigment, and it is known to cause various problems in manufacturing processes, ink products, and the like.
For example, dispersions containing pigments composed of fine particles often show high viscosity, so it is difficult not only to take out and transport products from the disperser after the dispersion process, but also to cause gelation during storage and difficult to use It may become. Furthermore, there is a possibility that the surface condition of the color-extracted product becomes poor, such as a decrease in gloss and a leveling failure.
In addition, when different types of pigments are used in combination, color unevenness due to aggregation or sedimentation or other phenomena may cause uneven color or markedly reduced coloring power.
さらに各種の印刷や塗工工程において、印刷機や塗工機のシリンダーやノズル等に付着したインキから溶剤が揮発することによって、インキが乾燥析出し皮膜が形成される。この乾燥インキが、インキに接触・混入した場合、乾燥インキがインキに再溶解しにくいため、両者が分離した状態でそのまま印刷等され、印刷物や塗工物の画像形成に支障をきたすことがある。これを避けるため、乾燥析出したインキが、インキに接触した際に速やかに溶解する適性（以下、溶剤乾燥後のインキ再溶解性又はインキ乾燥再溶解性という）が求められる。 Further, in various printing and coating processes, the solvent is volatilized from the ink adhering to the cylinders and nozzles of the printing machine and the coating machine, whereby the ink is dried and a film is formed. When this dry ink comes into contact with or mixes with the ink, the dry ink is difficult to redissolve in the ink, so that it is printed as it is in a state where both are separated, which may hinder the image formation of the printed matter or the coated product. . In order to avoid this, suitability is required for the ink that has been dried and deposited to dissolve quickly when it comes into contact with the ink (hereinafter referred to as ink redissolvability after solvent drying or ink dry resolubility).
以上の種々の問題点を解決するために、古くは特許文献１、特許文献２、特許文献３および特許文献４等において顔料を安定して分散させる方法が提案されている。また、種々のワニスに対して顔料を母体骨格として側鎖に酸性基や塩基性基を置換基として有する有機色素誘導体を分散剤として混合する方法が、特許文献５、特許文献６および特許文献７等に提案されているが、必ずしも満足な効果が得られず、さらに分散効果の優れた手法が望まれている。 In order to solve the above various problems, Patent Document 1, Patent Document 2, Patent Document 3, and Patent Document 4 have proposed methods for stably dispersing pigments. Further, Patent Document 5, Patent Document 6, and Patent Document 7 include a method of mixing, as a dispersant, an organic pigment derivative having a pigment as a base skeleton and a side chain having an acidic group or a basic group as a substituent for various varnishes. However, it is not always possible to obtain a satisfactory effect, and there is a demand for a technique with an excellent dispersion effect.
より分散安定性を改善するために、高分子の顔料分散剤を用いる方法についても提案されている。例えば、特許文献８〜１４には塩基性基を有する高分子顔料分散剤が開示されている。
しかしながら、低分子の有機色素誘導体や高分子の顔料分散剤を単独で用いてもその効果には限界があった。
In order to further improve the dispersion stability, a method using a polymeric pigment dispersant has also been proposed. For example, Patent Documents 8 to 14 disclose polymer pigment dispersants having a basic group.
However, even if a low molecular weight organic dye derivative or a high molecular pigment dispersant is used alone, its effect is limited.
また、特許文献１５には、低分子の有機色素誘導体と高分子の顔料分散剤の併用が提案されている。塩基性顔料分散剤として、幹ポリマー部にカチオン性官能基を有する櫛形グラフトポリマーが開示されているが、十分な顔料分散効果が得られないものであった。また、インキ乾燥再溶解性についても満足いくものではなかった。 Patent Document 15 proposes the combined use of a low molecular weight organic dye derivative and a high molecular pigment dispersant. As a basic pigment dispersant, a comb-shaped graft polymer having a cationic functional group in the trunk polymer portion is disclosed, but a sufficient pigment dispersion effect cannot be obtained. Also, the ink drying / dissolving property was not satisfactory.
本発明は、顔料分散性、流動性、保存安定性、乾燥再溶解性に優れたインキ、及びこれを与えうる顔料組成物の提供を目的とする。 An object of the present invention is to provide an ink excellent in pigment dispersibility, fluidity, storage stability, and dry redissolvability, and a pigment composition capable of providing the same.
本発明の第１の発明は、顔料と、下記一般式（１）で示される酸性官能基含有有機色素誘導体と、アミノ基または第４級アンモニウム塩を有するアルカリ可溶性樹脂と、有機溶剤とを含む顔料組成物であって、アミノ基または第４級アンモニウム基を有するアルカリ可溶性樹脂の塩基性基当量が３０００〜２００００ｇ／ｅｑであり、酸価が３０〜２００ｍｇＫＯＨ／ｇである顔料組成物であって、アミノ基または第４級アンモニウム塩を有するアルカリ可溶性樹脂が、アミノアルキル基含有不飽和カルボン酸エステルまたはアミノ基の第４級アンモニウム塩を有するエチレン性不飽和単量体と、カルボキシル基を有するエチレン性不飽和単量体との共重合体である顔料組成物である。
（Ｐ−Ｘ）-［Ｎ（Ｒ１，Ｒ２，Ｒ３，Ｒ４）］+ 一般式（１）
(式中、Ｐはアゾ系、ベンズイミダソロン系、フタロシアニン系、キナクリドン系、アントラキノン系、ジオキサジン系、ジケトビロロピロール系、キノフタロン系、イソインドリノン系、イソインドリン系、ペリレン系、ペリノン系、ブラバンスロン系、ピランスロン系、及び、アソスラピリミジン系から選ばれる少なくとも一種の有機色素残基を、Ｘはスルホン酸基またはカルボン酸基を、Ｒ１は炭素数５〜２０のアルキル基を、Ｒ２，Ｒ３，Ｒ４はそれぞれ独立に水素原子または炭素数１〜２０のアルキル基を表す。)
The first invention of the present invention includes a pigment, an acidic functional group-containing organic dye derivative represented by the following general formula (1), an alkali-soluble resin having an amino group or a quaternary ammonium salt, and an organic solvent. A pigment composition, wherein the alkali-soluble resin having an amino group or a quaternary ammonium group has a basic group equivalent of 3000 to 20000 g / eq and an acid value of 30 to 200 mgKOH / g. An alkali-soluble resin having an amino group or a quaternary ammonium salt is an ethylenically unsaturated monomer having an aminoalkyl group-containing unsaturated carboxylic acid ester or a quaternary ammonium salt of an amino group, and an ethylene having a carboxyl group It is a pigment composition which is a copolymer with a polymerizable unsaturated monomer.
(PX) - [N (R1, R2, R3, R4)] + General formula (1)
(In the formula, P represents azo, benzimidazolone, phthalocyanine, quinacridone, anthraquinone, dioxazine, diketopyrrolopyrrole, quinophthalone, isoindolinone, isoindoline, perylene, perinone. , At least one organic dye residue selected from Bravanthrone, pyranthrone, and asosurapyrimidine, X is a sulfonic acid group or carboxylic acid group, R1 is an alkyl group having 5 to 20 carbon atoms, R2 , R3 and R4 each independently represents a hydrogen atom or an alkyl group having 1 to 20 carbon atoms.)
第２の発明は、顔料１００重量部に対して、一般式（１）で示される酸性官能基含有有機色素誘導体が１〜３０重量部、アミノ基または第４級アンモニウム塩を有するアルカリ可溶性樹脂が１〜１００重量部である第１の発明に記載の顔料組成物である。
The second invention is an alkali-soluble resin having 1 to 30 parts by weight of an acidic functional group-containing organic dye derivative represented by the general formula (1) and an amino group or a quaternary ammonium salt with respect to 100 parts by weight of the pigment. It is a pigment composition as described in 1st invention which is 1-100 weight part.
第３の発明は、顔料が、カーボンブラックである第１又は第２の発明に記載の顔料組成物である。 A third invention is the pigment composition according to the first or second invention, wherein the pigment is carbon black.
第４の発明は、第１ないし第３の発明いずれかに記載の顔料組成物を含むインキである。 A fourth invention is an ink containing the pigment composition according to any one of the first to third inventions.
本発明の顔料組成物は、顔料と、一般式（１）で示される酸性官能基含有有機色素誘導体と、アミノ基または第４級アンモニウム塩を有するアルカリ可溶性樹脂と、有機溶剤とを含む顔料組成物であって、アミノ基または第４級アンモニウム基を有するアルカリ可溶性樹脂の塩基性基当量が３０００〜２００００ｇ／ｅｑであり、酸価が３０〜２００ｍｇＫＯＨ／ｇなので従来得られなかった顔料分散性が得られると共に、アルカリ可溶性が良好なので分散安定性も良好である。
The pigment composition of the present invention includes a pigment, an acidic functional group-containing organic dye derivative represented by the general formula (1), an alkali-soluble resin having an amino group or a quaternary ammonium salt, and an organic solvent. The basic group equivalent of an alkali-soluble resin having an amino group or a quaternary ammonium group is 3000 to 20000 g / eq, and the acid value is 30 to 200 mg KOH / g. In addition to being obtained, the alkali-solubility is good, so that the dispersion stability is also good.
本発明の顔料組成物は、顔料１００重量部に対して、一般式（１）で示される酸性官能基含有有機色素誘導体が１〜３０重量部、アミノ基または第４級アンモニウム塩を有するアルカリ可溶性樹脂が１〜１００重量部なので、更に良好な分散性が得られる。
The pigment composition of the present invention is an alkali-soluble compound having 1 to 30 parts by weight of an acidic functional group-containing organic dye derivative represented by the general formula (1) and an amino group or a quaternary ammonium salt based on 100 parts by weight of the pigment. Since the resin is 1 to 100 parts by weight, even better dispersibility can be obtained.
本発明の顔料組成物は、カーボンブラックの分散性に特に優れる。 The pigment composition of the present invention is particularly excellent in carbon black dispersibility.
本発明のインキは上記顔料組成物を含むので、従来得られなかった顔料分散性を有する。よって流動性及び分散安定性が良好である。更に保存安定性も良好である。また、インキ乾燥後における顔料間の凝集力が弱いので、乾燥インキがインキと再接触しても速やかにインキに溶解できるため、印刷ならびに塗加工を安定して歩留まりよく実施することができる。 Since the ink of the present invention contains the above pigment composition, it has a pigment dispersibility that has not been obtained conventionally. Therefore, fluidity and dispersion stability are good. Furthermore, the storage stability is also good. Further, since the cohesive force between the pigments after ink drying is weak, even if the dried ink re-contacts with the ink, it can be quickly dissolved in the ink, so that printing and coating can be performed stably and with high yield.
＜顔料＞
本発明で用いられる顔料とは、インキ等に使用される公知の有機顔料や無機顔料である。有機顔料としては溶性アゾ顔料、不溶性アゾ顔料、フタロシアニン顔料、キナクリドン顔料、イソインドリノン顔料、イソインドリン顔料、ペリレン顔料、ペリノン顔料、ジオキサジン顔料、アントラキノン顔料、ジアンスラキノニル顔料、アンスラピリミジン顔料、アンサンスロン顔料、インダンスロン顔料、フラバンスロン顔料、ピランスロン顔料、ジケトピロロピロール顔料等が挙げられる。さらに具体的な例をカラーインデックスのジェネリックネームで示すと、ピグメントブラック７、ピグメントブルー１５，１５：１，１５：３，１５：４，１５：６，６０、ピグメントグリーン７，３６，ピグメントレッド９，４８，４９，５２，５３，５７，９７，１２２，１４４，１４６，１４９，１６６，１６８，１７７，１７８，１７９，１８５，２０６，２０７，２０９，２２０，２２１，２３８，２４２，２５４，２５５、ピグメントバイオレット１９，２３，２９，３０，３７，４０，５０、ピグメントイエロー１２，１３，１４，１７，２０，２４，７４，８３，８６，９３，９４，９５，１０９，１１０，１１７，１２０，１２５，１２８，１３７，１３８，１３９，１４７，１４８，１５０，１５１，１５４，１５５，１６６，１６８，１８０，１８５、ピグメントオレンジ１３，３６，３７、３８，４３，５１，５５，５９，６１，６４，７１，７４等が挙げられる。
<Pigment>
The pigment used in the present invention is a known organic pigment or inorganic pigment used for ink or the like. Organic pigments include soluble azo pigments, insoluble azo pigments, phthalocyanine pigments, quinacridone pigments, isoindolinone pigments, isoindoline pigments, perylene pigments, perinone pigments, dioxazine pigments, anthraquinone pigments, dianthraquinonyl pigments, anthrapyrimidine pigments, ansan Examples include a throne pigment, an indanthrone pigment, a flavanthrone pigment, a pyranthrone pigment, and a diketopyrrolopyrrole pigment. More specific examples are represented by generic names of color indexes: Pigment Black 7, Pigment Blue 15, 15: 1, 15: 3, 15: 4, 15: 6, 60, Pigment Green 7, 36, Pigment Red 9 48, 49, 52, 53, 57, 97, 122, 144, 146, 149, 166, 168, 177, 178, 179, 185, 206, 207, 209, 220, 221, 238, 242, 254, 255 Pigment Violet 19, 23, 29, 30, 37, 40, 50, Pigment Yellow 12, 13, 14, 17, 20, 24, 74, 83, 86, 93, 94, 95, 109, 110, 117, 120 , 125, 128, 137, 138, 139, 147, 148, 150, 151, 154, 155 66,168,180,185, Pigment Orange 13,36,37,38,43,51,55,59,61,64,71,74, and the like.
無機顔料としては酸化チタン、亜鉛華、硫化亜鉛、鉛白、炭酸カルシウム、沈降性硫酸バリウム、ホワイトカーボン、アルミナホワイト、カオリンクレー、タルク、ベントナイト、黒色酸化鉄、カドミウムレッド、べんがら、モリブデンレッド、モリブデートオレンジ、クロムバーミリオン、黄鉛、カドミウムイエロー、黄色酸化鉄、チタンイエロー、酸化クロム、ビリジアン、チタンコバルトグリーン、コバルトグリーン、コバルトクロムグリーン、ビクトリアグリーン、群青、紺青、コバルトブルー、セルリアンブルー、コバルトシリカブルー、コバルト亜鉛シリカブルー、マンガンバイオレット、コバルトバイオレット、またはアセチレンブラック、チャンネルブラック、ファーネスブラック等のカーボンブラックが挙げられる。カーボンブラックについては中性、酸性、塩基性いずれのカーボンブラックも使用することができる。本発明において顔料がカーボンブラックの場合、著しい分散効果が得られる。 Inorganic pigments include titanium oxide, zinc white, zinc sulfide, lead white, calcium carbonate, precipitated barium sulfate, white carbon, alumina white, kaolin clay, talc, bentonite, black iron oxide, cadmium red, brown, molybdenum red, molybdenum Date orange, chrome vermilion, yellow lead, cadmium yellow, yellow iron oxide, titanium yellow, chromium oxide, viridian, titanium cobalt green, cobalt green, cobalt chrome green, Victoria green, ultramarine, bitumen, cobalt blue, cerulean blue, cobalt Examples thereof include silica blue, cobalt zinc silica blue, manganese violet, cobalt violet, and carbon black such as acetylene black, channel black, and furnace black. As for carbon black, neutral, acidic, or basic carbon black can be used. In the present invention, when the pigment is carbon black, a remarkable dispersion effect is obtained.
＜一般式（１）で示される酸性官能基含有有機色素誘導体＞
本発明で用いられる酸性官能基含有有機色素誘導体は、下記一般式（１）で示される。
（Ｐ−Ｘ）−［Ｎ（Ｒ１，Ｒ２，Ｒ３，Ｒ４）］＋ 一般式（１）
(式中、Ｐはアゾ系、ベンズイミダソロン系、フタロシアニン系、キナクリドン系、アントラキノン系、ジオキサジン系、ジケトビロロピロール系、キノフタロン系、イソインドリノン系、イソインドリン系、ペリレン系、ペリノン系、ブラバンスロン系、ピランスロン系、及び、アソスラピリミジン系から選ばれる少なくとも一種の有機色素残基を、Ｘはスルホン酸基またはカルボン酸基を、Ｒ１は炭素数５〜２０のアルキル基を、Ｒ２、Ｒ３、Ｒ４はそれぞれ独立に水素原子または炭素数１〜２０のアルキル基を表す。)
<Acid functional group-containing organic dye derivative represented by the general formula (1)>
The acidic functional group-containing organic dye derivative used in the present invention is represented by the following general formula (1).
(PX) - [N (R1, R2, R3, R4)] + General formula (1)
(In the formula, P represents azo, benzimidazolone, phthalocyanine, quinacridone, anthraquinone, dioxazine, diketopyrrolopyrrole, quinophthalone, isoindolinone, isoindoline, perylene, perinone. , At least one organic dye residue selected from Bravanthrone, pyranthrone, and asosurapyrimidine, X is a sulfonic acid group or carboxylic acid group, R1 is an alkyl group having 5 to 20 carbon atoms, R2 , R3 and R4 each independently represents a hydrogen atom or an alkyl group having 1 to 20 carbon atoms.)
顔料組成物において用いられる顔料の化学構造と、一般式（１）で示される酸性官能基含有有機色素誘導体における有機色素残基の化学構造は必ずしも一致しなければいけないものではない。しかし、最終的に製造されるインキの色相を考慮すると、分散する顔料が黄色系顔料の場合は黄色系の有機色素誘導体、赤系顔料の場合は赤系の有機色素誘導体、青系顔料の際には青系の有機色素誘導体のように、分散する顔料と色相が近いもの、もしくは無色のものを使用した方が色相的に優れた顔料組成物を製造することができる。 The chemical structure of the pigment used in the pigment composition and the chemical structure of the organic dye residue in the acidic functional group-containing organic dye derivative represented by the general formula (1) do not necessarily have to match. However, in consideration of the hue of the ink to be finally produced, when the pigment to be dispersed is a yellow pigment, when it is a yellow organic pigment derivative, when it is a red pigment, it is a red organic pigment derivative or a blue pigment. In the case of using a pigment having a hue close to that of the pigment to be dispersed or a colorless pigment, such as a blue organic dye derivative, a pigment composition excellent in hue can be produced.
本発明で用いられる、一般式(１)で示される酸性官能基含有有機色素誘導体は、スルホン酸基またはカルボン酸基を導入した有機色素誘導体をアミンで造塩させたものであり、これによって初めて顔料分散への著しい効果をもたらすものである。この誘導体の置換基がスルホン酸またはカルボン酸のような酸性性状のままでは、その効果は期待できない。 The acidic functional group-containing organic dye derivative represented by the general formula (1) used in the present invention is obtained by salting an organic dye derivative having a sulfonic acid group or a carboxylic acid group introduced with an amine. It has a remarkable effect on pigment dispersion. If the substituent of this derivative remains in an acidic state such as sulfonic acid or carboxylic acid, the effect cannot be expected.
アミンの例としてはオクチルアミン、ドデシルアミン等の1級アミン、ジオレイルアミン、ジスナアリルアミン等の２級アミン、ジメチルラウリルアミン、ジメチルステアリルアミン等の３級アミン、トリメチルアンモニウム、ジメチルジステアリルアンモニウム等の４級アンモニウム等が挙げられる。１級アミンと４級アミンが好ましい。 Examples of amines include primary amines such as octylamine and dodecylamine, secondary amines such as dioleylamine and disnaallylamine, tertiary amines such as dimethyllaurylamine and dimethylstearylamine, trimethylammonium and dimethyldistearylammonium. Quaternary ammonium etc. are mentioned. Primary amines and quaternary amines are preferred.
＜アミノ基または第４級アンモニウム塩を有するアルカリ可溶性樹脂＞
本発明で用いられるアミノ基または第４級アンモニウム塩を有するアルカリ可溶性樹脂（以下、アルカリ可溶性樹脂という）は、（Ａ）アミノ基または第４級アンモニウム塩を有するエチレン性不飽和単量体と、（Ａ）以外のエチレン性不飽和単量体を共重合することにより得ることができる。
<Alkali-soluble resin having amino group or quaternary ammonium salt>
The alkali-soluble resin having an amino group or quaternary ammonium salt used in the present invention (hereinafter referred to as alkali-soluble resin) is (A) an ethylenically unsaturated monomer having an amino group or quaternary ammonium salt; It can be obtained by copolymerizing ethylenically unsaturated monomers other than (A).
アミノ基を有するエチレン性不飽和単量体としては、アミノアルキル基含有不飽和カルボン酸エステル等が挙げられる。
The ethylenically unsaturated monomer having an amino group, and a aminoalkyl group-containing unsaturated carboxylic acid ester.
アミノアルキル基含有不飽和カルボン酸エステルとしては、２−アミノエチル（メタ）アクリレート、２−Ｎ−メチルアミノエチル（メタ）アクリレート、２−Ｎ−エチルアミノエチル（メタ）アクリレート、２−Ｎ，Ｎ−ジメチルアミノエチル（メタ）アクリレート、２−Ｎ，Ｎ−ジエチルアミノエチル（メタ）アクリレート、２−アミノプロピル（メタ）アクリレート、２−Ｎ−メチルアミノプロピル（メタ）アクリレート、２−Ｎ−エチルアミノプロピル（メタ）アクリレート、２−Ｎ，Ｎ−ジメチルアミノプロピル（メタ）アクリレート、２−Ｎ，Ｎ−ジエチルアミノプロピル（メタ）アクリレート、３−アミノプロピル（メタ）アクリレート、３−Ｎ−メチルアミノプロピル（メタ）アクリレート、３−Ｎ−エチルアミノプロピル（メタ）アクリレート、３−Ｎ，Ｎ−ジメチルアミノプロピル（メタ）アクリレート、３−Ｎ，Ｎ−ジエチルアミノプロピル（メタ）アクリレート等が挙げられる。 As the aminoalkyl group-containing unsaturated carboxylic acid ester, 2-aminoethyl (meth) acrylate, 2-N-methylaminoethyl (meth) acrylate, 2-N-ethylaminoethyl (meth) acrylate, 2-N, N -Dimethylaminoethyl (meth) acrylate, 2-N, N-diethylaminoethyl (meth) acrylate, 2-aminopropyl (meth) acrylate, 2-N-methylaminopropyl (meth) acrylate, 2-N-ethylaminopropyl (Meth) acrylate, 2-N, N-dimethylaminopropyl (meth) acrylate, 2-N, N-diethylaminopropyl (meth) acrylate, 3-aminopropyl (meth) acrylate, 3-N-methylaminopropyl (meth) ) Acrylate, 3-N-ethylaminopropyl Meth) acrylate, 3-N, N- dimethylaminopropyl (meth) acrylate, 3-N, N- diethylaminopropyl (meth) acrylate.
第４級アンモニウム塩を有するエチレン性不飽和単量体とは、１分子中にひとつの第４級アンモニウム基、ひとつの（メタ）アクリロイル基を含有する単量体である。具体的には、２−ヒドロキシ−３（メタ）アクリルオキシプロピルトリメチルアンモニウムクロライド、２−ヒドロキシ−３（メタ）アクリルオキシプロピルトリエタノールアンモニウムクロライド、２−ヒドロキシ−３（メタ）アクリルオキシプロピルジメチルベンジルアンモニウム等が挙げられる。
The ethylenically unsaturated monomer having a quaternary ammonium salt is a monomer containing one quaternary ammonium group and one (meth) acryloyl group in one molecule. Specifically, 2-hydroxy-3 (meth) acryloxypropyltrimethylammonium chloride, 2-hydroxy-3 (meth) acryloxypropyltriethanolammonium chloride, 2-hydroxy-3 (meth) acryloxypropyldimethylbenzylammonium Etc.
前記（Ａ）アミノ基または第４級アンモニウム塩を有するエチレン性不飽和単量体は、単独でまたは２種以上を混合して使用することができる。
The (A) ethylenically unsaturated monomer having an amino group or a quaternary ammonium salt can be used alone or in admixture of two or more.
（Ａ）以外のエチレン性不飽和単量体としては、カルボキシル基を有するエチレン性不飽和単量体等が挙げられる。
カルボキシル基を有するエチレン性不飽和単量体として（メタ）アクリル酸、クロトン酸、α−クロルアクリル酸、エタクリル酸、けい皮酸、こはく酸モノ〔２−（メタ）アクリロイルオキシエチル〕、フタル酸モノ〔２−（メタ）アクリロイルオキシエチル〕、Ω−カルボキシポリカプロラクトンモノ（メタ）アクリレート等のモノカルボン酸類；マレイン酸、無水マレイン酸、フマル酸、イタコン酸、無水イタコン酸、シトラコン酸、無水シトラコン酸、メサコン酸等のジカルボン酸（無水物）類；３価以上の多価カルボン酸（無水物）類等を挙げることができる。
Examples of the ethylenically unsaturated monomer other than (A) include an ethylenically unsaturated monomer having a carboxyl group.
Ethylenically unsaturated monomers having a carboxyl group (meth) acrylic acid, crotonic acid, α-chloroacrylic acid, ethacrylic acid, cinnamic acid, succinic acid mono [2- (meth) acryloyloxyethyl], phthalic acid Monocarboxylic acids such as mono [2- (meth) acryloyloxyethyl], Ω-carboxypolycaprolactone mono (meth) acrylate; maleic acid, maleic anhydride, fumaric acid, itaconic acid, itaconic anhydride, citraconic acid, citraconic anhydride Examples thereof include dicarboxylic acids (anhydrides) such as acids and mesaconic acids; trivalent or higher polyvalent carboxylic acids (anhydrides).
これらのカルボキシル基を有するエチレン性不飽和単量体のうち、（メタ）アクリル酸、こはく酸モノ〔２−（メタ）アクリロイルオキシエチル〕、Ω−カルボキシポリカプロラクトンモノ（メタ）アクリレート等が好ましい。 Of these ethylenically unsaturated monomers having a carboxyl group, (meth) acrylic acid, succinic acid mono [2- (meth) acryloyloxyethyl], Ω-carboxypolycaprolactone mono (meth) acrylate and the like are preferable.
（メタ）アクリル酸としては、炭素数１〜１８のアルキル基や水酸基を有する（メタ）アクリル酸エステル等が挙げられる。
炭素数１〜１８のアルキル基を含有する（メタ）アクリル酸アルキルエステルの具体例としては、メチル（メタ）アクリレート、エチル（メタ）アクリレート、ｎ−プロピル（メタ）アクリレート、イソプロピル（メタ）アクリレート、ｎ−ブチル（メタ）アクリレート、イソブチル（メタ）アクリレート、ヘキシル（メタ）アクリレート、２−エチルヘキシル（メタ）アクリレート、イソデシル（メタ）アクリレート、ラウリル（メタ）アクリレート、ステアリル（メタ）アクリレート等が挙げられる。
Examples of (meth) acrylic acid include (meth) acrylic acid esters having an alkyl group having 1 to 18 carbon atoms and a hydroxyl group.
Specific examples of the (meth) acrylic acid alkyl ester containing an alkyl group having 1 to 18 carbon atoms include methyl (meth) acrylate, ethyl (meth) acrylate, n-propyl (meth) acrylate, isopropyl (meth) acrylate, Examples include n-butyl (meth) acrylate, isobutyl (meth) acrylate, hexyl (meth) acrylate, 2-ethylhexyl (meth) acrylate, isodecyl (meth) acrylate, lauryl (meth) acrylate, stearyl (meth) acrylate, and the like.
水酸基を有する（メタ）アクリル酸エステルの具体例としては、２−ヒドロキシエチル（メタ）アクリレート、２−ヒドロキシプロピル（メタ）アクリレート、２−ヒドロキシブチル（メタ）アクリレート等が挙げられる。 Specific examples of the (meth) acrylic acid ester having a hydroxyl group include 2-hydroxyethyl (meth) acrylate, 2-hydroxypropyl (meth) acrylate, 2-hydroxybutyl (meth) acrylate and the like.
上記以外の（メタ）アクリル酸エステルの具体例としては、メトキシジエチレングリコール（メタ）アクリレート、メトキシポリエチレングリコール（メタ）アクリレート、メトキシプロピレングリコール（メタ）アクリレート、メトキシジプロピレングリコール（メタ）アクリレート、メトキシポリプロピレングリコール（メタ）アクリレート、ｎ−ブトキシエチレングリコール（メタ）アクリレート、２−フェノキシエチル（メタ）アクリレート、フェノキシポリエチレングリコール（メタ）アクリレート、トリオキシエチレンノニルフェノール（メタ）アクリレート等が挙げられる。 Specific examples of (meth) acrylic acid esters other than the above include methoxydiethylene glycol (meth) acrylate, methoxypolyethylene glycol (meth) acrylate, methoxypropylene glycol (meth) acrylate, methoxydipropylene glycol (meth) acrylate, methoxypolypropylene glycol (Meth) acrylate, n-butoxyethylene glycol (meth) acrylate, 2-phenoxyethyl (meth) acrylate, phenoxypolyethylene glycol (meth) acrylate, trioxyethylene nonylphenol (meth) acrylate, and the like.
上記の（Ａ）以外のエチレン性不飽和単量体は、単独でまたは２種以上を混合して使用することができる。 The ethylenically unsaturated monomers other than the above (A) can be used alone or in admixture of two or more.
アルカリ可溶性樹脂は、溶液重合法や塊状重合法で得ることができる。溶液重合法の場合には、（Ａ）アミノ基または第４級アンモニウム塩を有するエチレン性不飽和単量体と、（Ａ）以外のエチレン性不飽和単量体を、重合開始剤の存在下、適当な不活性溶媒中で重合して製造される。反応温度は７０〜１５０℃、さらに好ましくは８０〜１３０℃である。反応時間は１〜１５時間、特に４〜８時間が望ましい。
The alkali-soluble resin can be obtained by a solution polymerization method or a bulk polymerization method. In the case of the solution polymerization method, (A) an ethylenically unsaturated monomer having an amino group or a quaternary ammonium salt and an ethylenically unsaturated monomer other than (A) are added in the presence of a polymerization initiator. It is produced by polymerization in a suitable inert solvent. The reaction temperature is 70 to 150 ° C, more preferably 80 to 130 ° C. The reaction time is preferably 1 to 15 hours, particularly 4 to 8 hours.
重合開始剤には、アゾビスイソブチロニトリル、ジメチルアゾビスイソブチレート等のアゾ系化合物、ラウロイルパーオキサイド、ジイソプロピルベンゼンハイドロパーオキサイド等の有機過酸化物が挙げられる。 Examples of the polymerization initiator include azo compounds such as azobisisobutyronitrile and dimethylazobisisobutyrate, and organic peroxides such as lauroyl peroxide and diisopropylbenzene hydroperoxide.
アルカリ可溶性樹脂の塩基性基当量は３０００〜２００００ｇ／ｅｑである。４０００〜５０００が好ましい。塩基性基当量が３０００ｇ／ｅｑ未満では塩基性基量が多すぎるため、期待した分散効果が得られない。また、２００００ｇ／ｅｑより大きいと、一分子中の塩基性基量が少なすぎるために、酸性基含有有機色素誘導体と相互作用できず、分散効果が得られない。 The basic group equivalent of the alkali-soluble resin is 3000 to 20000 g / eq. 4000 to 5000 are preferred. If the basic group equivalent is less than 3000 g / eq, the amount of the basic group is too large, so that the expected dispersion effect cannot be obtained. On the other hand, if it is larger than 20000 g / eq, the amount of the basic group in one molecule is too small, so that it cannot interact with the acidic group-containing organic dye derivative and a dispersion effect cannot be obtained.
また、本発明でいうアルカリ可溶性樹脂とは、酸価が３０ｍｇＫＯＨ／ｇ以上の樹脂をいう。本発明で用いられるアルカリ可溶性樹脂の酸価は３０〜２００ｍｇＫＯＨ／ｇである。５０〜１５０ｍｇＫＯＨ／ｇがより好ましく、６０〜８０ｍｇＫＯＨ／ｇが特に好ましい。酸価が３０ｍｇＫＯＨ／ｇ未満ではアルカリ可溶性が低く、酸価が２００ｍｇＫＯＨ／ｇを超えるとアルカリ可溶性能が高すぎるため、組成物の分散安定性が悪くなる。
酸価は、カルボキシル基を有するエチレン性不飽和単量体により調整できる。尚、本発明における酸価はＪIＳ Ｋ ００７０（１９９６年）に基づいて測定したものである。
The alkali-soluble resin as used in the present invention refers to a resin having an acid value of 30 mgKOH / g or more. The acid value of the alkali-soluble resin used in the present invention is 30 to 200 mgKOH / g. 50 to 150 mgKOH / g is more preferable, and 60 to 80 mgKOH / g is particularly preferable. When the acid value is less than 30 mg KOH / g, the alkali solubility is low, and when the acid value exceeds 200 mg KOH / g, the alkali solubility is too high, so that the dispersion stability of the composition is deteriorated.
The acid value can be adjusted by an ethylenically unsaturated monomer having a carboxyl group. The acid value in the present invention is measured based on JIS K 0070 (1996).
アルカリ可溶性樹脂の重量平均分子量は、ＧＰＣによるポリスチレン換算の重量平均分子量で３０００〜１０００００が好ましい。１００００〜５００００が特に好ましい。分子量が３０００より低い場合には、塗膜の物性が低下する傾向がある。１０００００より高い場合には、顔料分散体の粘度が高くなりすぎ取り扱いにくい傾向がある。分子量はアルキルメルカプタン等の重合調整剤により容易に調節される。 The weight average molecular weight of the alkali-soluble resin is preferably 3000 to 100,000 in terms of polystyrene equivalent weight average molecular weight by GPC. 10,000 to 50,000 is particularly preferable. When the molecular weight is lower than 3000, the physical properties of the coating film tend to decrease. If it is higher than 100,000, the viscosity of the pigment dispersion tends to be too high and difficult to handle. The molecular weight is easily adjusted by a polymerization regulator such as an alkyl mercaptan.
＜有機溶剤＞
本発明の顔料組成物において用いられる有機溶剤としては、インキ等に使用される有機溶剤が利用できる。具体的な例としては、メチルアルコール、エチルアルコール、ｎ−プロピルアルコール、イソプロピルアルコール、ｎ−ブチルアルコール等のアルコール類、アセトン、メチルエチルケトン、メチル−n-プロピルケトン、メチルイソプロピルケトン、メチル−n-ブチルケトン、メチルイソブチルケトン、メチル−n-アミルケトン、メチルイソアミルケトン、ジエチルケトン、エチル−n-プロピルケトン、エチルイソプロピルケトン、エチル−n-ブチルケトン、エチルイソブチルケトン、ジ−n-プロピルケトン、ジイソブチルケトン、シクロヘキサノン、メチルシクロヘキサノン、イソホロン等のケトン類、酢酸メチル、酢酸エチル、酢酸−ｎ−プロピル、酢酸イソプロピル、酢酸−ｎ−ブチル、酢酸イソブチル、酢酸ヘキシル、酢酸オクチル、乳酸メチル、乳酸プロピル、乳酸ブチル等のエステル類、エチレングリコール、エチレングリコールモノイソプロピルエーテル、エチレングリコールモノブチルエーテル、エチレングリコールモノヘキシルエーテル、ジエチレングリコールモノメチルエーテル、ジエチレングリコールモノエチルエーテル、ジエチレングリコールモノブチルエーテル、エチレングリコールジメチルエーテル、エチレングリコールジエチルエーテル、ジエチレングリコールジメチルエーテル、ジエチレングリコールジエチルエーテル、プロピレングリコール、プロピレングリコールモノメチルエーテル、プロピレングリコールモノエチルエーテル、プロピレングリコールモノプロピルエーテル、プロピレングリコールモノブチルエーテル、ジプロピレングリコールモノメチルエーテル、ジプロピレングリコールモノエチルエーテル、ジプロピレングリコールジプロピルエーテル、トリプロピレングリコールモノメチルエーテル等のグリコールおよびグリコールエーテル類、エチレングリコールモノメチルエーテルアセテート、エチレングリコールモノエチルエーテルアセテート、エチレングリコールモノブチルエーテルアセテート、ジエチレングリコールモノメチルエーテルアセテート、ジエチレングリコールモノエチルエーテルアセテート、ジエチレングリコールモノブチルエーテルアセテート、プロピレングリコールモノメチルエーテルアセテート、プロピレングリコールモノエチルエーテルアセテート、プロピレングリコールモノブチルエーテルアセテート、ジプロピレングリコールモノメチルエーテルアセテート等のグリコールアセテート類、ｎ−ヘキサン、イソヘキサン、ｎ−ノナン、イソノナン、ドデカン、イソドデカン等の飽和炭水素類、１−ヘキセン、１−ヘプテン、１−オクテン等の不飽和炭化水素類、シクロヘキサン、シクロヘプタン、シクロオクタン、シクロデカン、デカリン等の環状飽和炭化水素類、シクロヘキセン、シクロヘプテン、シクロオクテン、１,１，３，５，７−シクロオクタテトラエン、シクロドデセン等の環状不飽和炭化水素類、ベンゼン、トルエン、キシレン等の芳香族炭化水素類等が挙げられる。これらの有機溶剤は単独で使用しても、２種類以上を混合して使用しても良い。
<Organic solvent>
As the organic solvent used in the pigment composition of the present invention, an organic solvent used in ink or the like can be used. Specific examples include alcohols such as methyl alcohol, ethyl alcohol, n-propyl alcohol, isopropyl alcohol, n-butyl alcohol, acetone, methyl ethyl ketone, methyl n-propyl ketone, methyl isopropyl ketone, methyl n-butyl ketone. , Methyl isobutyl ketone, methyl-n-amyl ketone, methyl isoamyl ketone, diethyl ketone, ethyl n-propyl ketone, ethyl isopropyl ketone, ethyl n-butyl ketone, ethyl isobutyl ketone, di-n-propyl ketone, diisobutyl ketone, cyclohexanone , Ketones such as methylcyclohexanone, isophorone, methyl acetate, ethyl acetate, acetic acid-n-propyl, isopropyl acetate, acetic acid-n-butyl, isobutyl acetate, hexyl acetate, octyl acetate, milk Esters such as methyl, propyl lactate and butyl lactate, ethylene glycol, ethylene glycol monoisopropyl ether, ethylene glycol monobutyl ether, ethylene glycol monohexyl ether, diethylene glycol monomethyl ether, diethylene glycol monoethyl ether, diethylene glycol monobutyl ether, ethylene glycol dimethyl ether, ethylene Glycol diethyl ether, diethylene glycol dimethyl ether, diethylene glycol diethyl ether, propylene glycol, propylene glycol monomethyl ether, propylene glycol monoethyl ether, propylene glycol monopropyl ether, propylene glycol monobutyl ether, dipropylene glycol Glycols and glycol ethers such as nomethyl ether, dipropylene glycol monoethyl ether, dipropylene glycol dipropyl ether, tripropylene glycol monomethyl ether, ethylene glycol monomethyl ether acetate, ethylene glycol monoethyl ether acetate, ethylene glycol monobutyl ether acetate, Diethylene glycol monomethyl ether acetate, diethylene glycol monoethyl ether acetate, diethylene glycol monobutyl ether acetate, propylene glycol monomethyl ether acetate, propylene glycol monoethyl ether acetate, propylene glycol monobutyl ether acetate, dipropylene glycol monomethyl ether Glycol acetates such as teracetate, saturated hydrocarbons such as n-hexane, isohexane, n-nonane, isononane, dodecane and isododecane, unsaturated hydrocarbons such as 1-hexene, 1-heptene and 1-octene, cyclohexane Cyclic saturated hydrocarbons such as cycloheptane, cyclooctane, cyclodecane and decalin, cyclic unsaturated hydrocarbons such as cyclohexene, cycloheptene, cyclooctene, 1,1,3,5,7-cyclooctatetraene and cyclododecene, Aromatic hydrocarbons such as benzene, toluene, xylene and the like. These organic solvents may be used alone or in combination of two or more.
＜顔料組成物＞
本発明の顔料組成物は、顔料と、一般式（１）で示される酸性官能基含有有機色素誘導体と、アルカリ可溶性樹脂と、有機溶剤とを含み、目的とする性状に合わせて公知の方法にて製造される。
<Pigment composition>
The pigment composition of the present invention contains a pigment, an acidic functional group-containing organic dye derivative represented by the general formula (1), an alkali-soluble resin, and an organic solvent, and is subjected to a known method according to the intended properties. Manufactured.
例えば、アルカリ可溶性樹脂と有機溶剤中に、一般式（１）で示される酸性官能基含有有機色素誘導体と顔料を投入し、ハイスピードミキサー等で均一になるまで撹拌混合した後、横型サンドミル、縦型サンドミル、アニュラー型サンドミル等のビーズミルやロールミル、メディアレス分散機等の種々の分散機を用いて分散して製造することができる。
また、酸性官能基含有有機色素誘導体は顔料製造の際に予め添加しておいてもよい。
For example, an acidic functional group-containing organic dye derivative represented by the general formula (1) and a pigment are put into an alkali-soluble resin and an organic solvent, and stirred and mixed with a high-speed mixer or the like until a horizontal sand mill, It can be produced by dispersing using various dispersers such as a bead mill such as a sand mill and an annular sand mill, a roll mill, and a medialess disperser.
Further, the acidic functional group-containing organic dye derivative may be added in advance during the production of the pigment.
本発明の顔料組成物における各成分の配合は、顔料１００重量部に対して、一般式（１）で示される酸性官能基含有有機色素誘導体は１〜３０重量部、アルカリ可溶性樹脂は１〜１００重量部が好ましい。分散する顔料に対して一般式（１）で示される酸性官能基含有有機色素誘導体およびアルカリ可溶性樹脂の量が少なすぎると目的とする分散効果が得られず、多すぎると展色物の耐性が低下する傾向がある。 The blending of each component in the pigment composition of the present invention is 1 to 30 parts by weight of the acidic functional group-containing organic dye derivative represented by the general formula (1) and 1 to 100 of the alkali-soluble resin with respect to 100 parts by weight of the pigment. Part by weight is preferred. If the amount of the acidic functional group-containing organic dye derivative represented by the general formula (1) and the alkali-soluble resin is too small relative to the pigment to be dispersed, the intended dispersion effect cannot be obtained, and if it is too large, the resistance of the color-extracted product is reduced. There is a tendency to decrease.
＜インキ＞
本発明のインキは上記顔料組成物を含むものである。分散した顔料組成物に、必要に応じて有機溶剤やインキの添加剤として公知の成分を添加してもよい。
<Ink>
The ink of the present invention contains the above pigment composition. You may add a well-known component to the dispersed pigment composition as an additive of an organic solvent or an ink as needed.
本発明の顔料組成物およびインキには、その用途によって可塑剤、表面調整剤、紫外線防止剤、光安定化剤、酸化防止剤、帯電防止剤、アンチブロッキング剤、消泡剤、粘度調整剤、ワックス、界面活性剤、レベリング剤等の種々の添加剤を使用することができる。 The pigment composition and ink of the present invention include a plasticizer, a surface conditioner, an ultraviolet light inhibitor, a light stabilizer, an antioxidant, an antistatic agent, an antiblocking agent, an antifoaming agent, a viscosity modifier, depending on the use. Various additives such as waxes, surfactants and leveling agents can be used.
以下、実施例をあげて本発明を具体的に説明するが、本発明は実施例に特に限定されるものではない。なお、実施例中、「部」は「重量部」を表す。表１は、実施例等において用いられた酸性官能基含有有機色素誘導体を示し、表２は顔料組成物の組成と評価結果を示す。 EXAMPLES Hereinafter, the present invention will be specifically described with reference to examples, but the present invention is not particularly limited to the examples. In the examples, “part” represents “part by weight”. Table 1 shows the acidic functional group-containing organic dye derivatives used in Examples and the like, and Table 2 shows the composition and evaluation results of the pigment composition.
[アルカリ可溶性樹脂の製造]
製造例１
セパラブル４口フラスコに温度計、冷却管、窒素ガス導入管、攪拌装置を取り付けてメトキシプロピルアセテート３０７部を仕込み、９５℃に昇温し反応容器内を窒素置換した後、滴下管よりｎ−ブチルメタクリレート２１０部、メチルメタクリレート１０３部、メタクリル酸３６部、ジメチルアミノメタクリレート１０．８部、２，２‘−アゾビスイソブチロニトリル１６．２部、メトキシプロピルアセテート１７７部の混合溶液を２時間かけて滴下した。滴下終了から２時間後に、２，２’−アゾビスイソブチロニトリル２．９部をメトキシプロピルアセテートに溶解した溶液を添加し、更に１時間反応を継続し、固形分４０％、重量平均分子量８７００のアルカリ可溶性樹脂Ａを得た。アルカリ可溶性樹脂Ａの塩基性当量は、４３６０ｇ／ｅｑ、酸価は６５ｍｇＫＯＨ／ｇであった。
[Manufacture of alkali-soluble resins]
Production Example 1
A separable four-necked flask was equipped with a thermometer, a condenser tube, a nitrogen gas inlet tube, and a stirrer, charged with 307 parts of methoxypropyl acetate, heated to 95 ° C., and purged with nitrogen in the reaction vessel. A mixed solution of 210 parts of methacrylate, 103 parts of methyl methacrylate, 36 parts of methacrylic acid, 10.8 parts of dimethylamino methacrylate, 16.2 parts of 2,2′-azobisisobutyronitrile and 177 parts of methoxypropyl acetate is taken over 2 hours. And dripped. Two hours after the completion of the dropwise addition, a solution of 2.9 parts of 2,2′-azobisisobutyronitrile dissolved in methoxypropyl acetate was added, and the reaction was further continued for 1 hour, with a solid content of 40% and a weight average molecular weight. 8700 alkali-soluble resin A was obtained. The basic equivalent of the alkali-soluble resin A was 4360 g / eq, and the acid value was 65 mgKOH / g.
製造例２
セパラブル４口フラスコに温度計、冷却管、窒素ガス導入管、攪拌装置を取り付けてメトキシプロピルアセテート３３０部を仕込み、８０℃に昇温し反応容器内を窒素置換した後、滴下管よりｎ−ブチルメタクリレート２０６部、メチルメタクリレート１０３部、メタクリル酸３６部、ジメチルアミノエチルメタクリレートメチルクロライド塩１４．４部、２‘−アゾビスイソブチロニトリル１４．４部、メトキシプロピルアセテート１７７部の混合溶液を２時間かけて滴下した。滴下終了から２時間後、２，２’−アゾビスイソブチロニトリル２．９部をメトキシプロピルアセテートに溶解した溶液を添加し、更に１時間反応を継続し、固形分４０％、重量平均分子量１５０００のアルカリ可溶性樹脂Ｂを得た。アルカリ可溶性樹脂Ｂの塩基性当量は、４２９０ｇ/ｅｑ、酸価は６５ｍｇＫＯＨ／ｇであった。
Production Example 2
A separable four-necked flask was equipped with a thermometer, a condenser tube, a nitrogen gas inlet tube, and a stirrer and charged with 330 parts of methoxypropyl acetate. The temperature was raised to 80 ° C. and the inside of the reaction vessel was purged with nitrogen. 2 parts of a mixed solution of 206 parts of methacrylate, 103 parts of methyl methacrylate, 36 parts of methacrylic acid, 14.4 parts of dimethylaminoethyl methacrylate methyl chloride salt, 14.4 parts of 2′-azobisisobutyronitrile and 177 parts of methoxypropyl acetate It was added dropwise over time. Two hours after the completion of the dropwise addition, a solution of 2.9 parts of 2,2′-azobisisobutyronitrile dissolved in methoxypropyl acetate was added, and the reaction was further continued for 1 hour, with a solid content of 40% and a weight average molecular weight. 15000 alkali-soluble resin B was obtained. The basic equivalent of the alkali-soluble resin B was 4290 g / eq, and the acid value was 65 mgKOH / g.
製造例３
セパラブル４口フラスコに温度計、冷却管、窒素ガス導入管、攪拌装置を取り付けてメトキシプロピルアセテート３０２部を仕込み、８０℃に昇温し反応容器内を窒素置換した後、滴下管よりｎ−ブチルメタクリレート２０３部、メチルメタクリレート１０７部、メタクリル酸３６部、ジエチルアミノエチルメタクリレート１４．４部、２，２‘−アゾビスイソブチロニトリル１６．２部、メトキシプロピルアセテート１７７部の混合溶液を２時間かけて滴下した。滴下終了から２時間後、２，２’−アゾビスイソブチロニトリル２．９部をメトキシプロピルアセテートに溶解した溶液を添加し、更に１時間反応を継続し、固形分４０％、重量平均分子量１７０００のアルカリ可溶性樹脂Ｃを得た。アルカリ可溶性樹脂Ｃの塩基性基当量は、４３６０ｇ／ｅｑ、酸価は６５ｍｇＫＯＨ／ｇであった。
Production Example 3
A separable four-necked flask was equipped with a thermometer, a condenser tube, a nitrogen gas inlet tube, and a stirrer and charged with 302 parts of methoxypropyl acetate. The temperature was raised to 80 ° C. and the inside of the reaction vessel was purged with nitrogen. A mixed solution of 203 parts of methacrylate, 107 parts of methyl methacrylate, 36 parts of methacrylic acid, 14.4 parts of diethylaminoethyl methacrylate, 16.2 parts of 2,2′-azobisisobutyronitrile and 177 parts of methoxypropyl acetate is taken over 2 hours. And dripped. Two hours after the completion of the dropwise addition, a solution of 2.9 parts of 2,2′-azobisisobutyronitrile dissolved in methoxypropyl acetate was added, and the reaction was further continued for 1 hour, with a solid content of 40% and a weight average molecular weight. 17000 alkali-soluble resin C was obtained. The basic group equivalent of the alkali-soluble resin C was 4360 g / eq, and the acid value was 65 mgKOH / g.
製造例４（比較製造例）
セパラブル４口フラスコに温度計、冷却管、窒素ガス導入管、攪拌装置を取り付けてメトキシプロピルアセテート３３０部を仕込み、８０℃に昇温し反応容器内を窒素置換した後、滴下管よりｎ−ブチルメタクリレート１８５部、メチルメタクリレート１０３部、メタクリル酸３６部、ジメチルアミノエチルメタクリレート３６部、２，２‘−アゾビスイソブチロニトリル１４．２部、メトキシプロピルアセテート１７７部の混合溶液を２時間かけて滴下した。滴下終了から２時間後、２，２’−アゾビスイソブチロニトリル０．６部をメトキシプロピルアセテートに溶解した溶液を添加し、更に１時間反応を継続し、固形分３０％、重量平均分子量１１４００のアルカリ可溶性樹脂Ｄを得た。アルカリ可溶性樹脂Ｄの塩基性基当量は、１３００ｇ／ｅｑ、酸価は６５ｍｇＫＯＨ／ｇであった。
Production Example 4 (Comparative Production Example)
A separable four-necked flask was equipped with a thermometer, a condenser tube, a nitrogen gas inlet tube, and a stirrer and charged with 330 parts of methoxypropyl acetate. The temperature was raised to 80 ° C. and the inside of the reaction vessel was purged with nitrogen. A mixed solution of 185 parts of methacrylate, 103 parts of methyl methacrylate, 36 parts of methacrylic acid, 36 parts of dimethylaminoethyl methacrylate, 14.2 parts of 2,2′-azobisisobutyronitrile and 177 parts of methoxypropyl acetate is taken over 2 hours. It was dripped. 2 hours after the completion of the dropwise addition, a solution of 0.6 part of 2,2′-azobisisobutyronitrile dissolved in methoxypropyl acetate was added, and the reaction was continued for another 1 hour, with a solid content of 30% and a weight average molecular weight. 11400 alkali-soluble resin D was obtained. The basic group equivalent of the alkali-soluble resin D was 1300 g / eq, and the acid value was 65 mgKOH / g.
製造例５（比較製造例）
セパラブル４口フラスコに温度計、冷却管、窒素ガス導入管、攪拌装置を取り付けてメトキシプロピルアセテート３０７部を仕込み、１２０℃に昇温し反応容器内を窒素置換した後、滴下管よりｎ−ブチルメタクリレート２１９部、メチルメタクリレート１０３部、メタクリル酸３６部、ジメチルアミノエチルメタクリレート１．８部、２，２‘−アゾビスイソブチロニトリル１８部、メトキシプロピルアセテート１７７部の混合溶液を２時間かけて滴下した。滴下終了してから２時間後、２，２’−アゾビスイソブチロニトリル２．９部をメトキシプロピルアセテートに溶解した溶液を添加し、更に１時間反応を継続し、固形分３０％、重量平均分子量６７００のアルカリ可溶性樹脂Ｅを得た。アルカリ可溶性樹脂Ｅの塩基性基当量は、２６２００ｇ／ｅｑ、酸価は６５ｍｇＫＯＨ／ｇであった。
Production Example 5 (Comparative Production Example)
A separable four-necked flask was equipped with a thermometer, a condenser tube, a nitrogen gas inlet tube, and a stirrer and charged with 307 parts of methoxypropyl acetate. The temperature was raised to 120 ° C. and the inside of the reaction vessel was purged with nitrogen. A mixed solution of 219 parts of methacrylate, 103 parts of methyl methacrylate, 36 parts of methacrylic acid, 1.8 parts of dimethylaminoethyl methacrylate, 18 parts of 2,2′-azobisisobutyronitrile and 177 parts of methoxypropyl acetate is taken over 2 hours. It was dripped. Two hours after the completion of the dropwise addition, a solution of 2.9 parts of 2,2′-azobisisobutyronitrile dissolved in methoxypropyl acetate was added, and the reaction was further continued for 1 hour. An alkali-soluble resin E having an average molecular weight of 6700 was obtained. The basic group equivalent of the alkali-soluble resin E was 26200 g / eq, and the acid value was 65 mgKOH / g.
[実施例１]
アルカリ可溶性樹脂Ａ１２．５部をエチレングリコールモノブチルエーテルアセテート（以下 ＢＧＡｃという）４７．５部に溶解後、有機色素誘導体Ａ５．０部およびＬＩＯＮＯＬ ＢＬＵＥ ＦＧ−７３５１（東洋インキ製造社製 銅フタロシアニン顔料）３５部を投入し、ハイスピードミキサーにて均一になるまで約３０分間撹拌混合した。次いで、０．６Ｌの横型サンドミルにてミルベース１ｋｇあたり１時間分散した。
得られた分散体５０部に対し、ジペンタエリスリトール・ヘキサアクリレート（以下ＤＰＨＡという）１５部、イルガキュア９０７（チバガイギー社製）２部、トルオール１００部及びメチルエチルケトン（以下ＭＥＫという）５０部を加えて顔料組成物を得た。
[Example 1]
After dissolving 12.5 parts of alkali-soluble resin A in 47.5 parts of ethylene glycol monobutyl ether acetate (hereinafter referred to as BGAc), organic dye derivative A 5.0 parts and LIONOL BLUE FG-7351 (copper phthalocyanine pigment manufactured by Toyo Ink Co., Ltd.) 35 The mixture was stirred and mixed with a high speed mixer for about 30 minutes until uniform. Subsequently, it was dispersed for 1 hour per 1 kg of the mill base in a 0.6 L horizontal sand mill.
To 50 parts of the resulting dispersion, 15 parts of dipentaerythritol hexaacrylate (hereinafter referred to as DPHA), 2 parts of Irgacure 907 (manufactured by Ciba Geigy), 100 parts of toluene and 50 parts of methyl ethyl ketone (hereinafter referred to as MEK) are added to the pigment A composition was obtained.
[実施例２]
実施例１におけるアルカリ可溶性樹脂Ａおよび有機色素誘導体Ａを、アルカリ可溶性樹脂Ｂおよび有機色素誘導体Ｂに代えて同様の方法にて分散した。
得られた分散体を用い、実施例１と同様にして顔料組成物を得た。
[Example 2]
The alkali-soluble resin A and the organic dye derivative A in Example 1 were dispersed in the same manner in place of the alkali-soluble resin B and the organic dye derivative B.
Using the obtained dispersion, a pigment composition was obtained in the same manner as in Example 1.
[実施例３]
アルカリ可溶性樹脂Ｃ１０．０部を乳酸ブチル６３．５部に溶解し、有機色素誘導体Ｃ１．５部およびＨＯＳＴＡＰＥＲＭ ＲＥＤ Ｅ５Ｂ ０２（クラリアント社製 キナクリドン顔料）２５部を投入してハイスピードミキサーにて均一になるまで約３０分間撹拌混合した後、０．６Ｌの横型サンドミルにてミルベース１ｋｇあたり１時間分散した。
得られた分散体を用い、実施例１と同様にして顔料組成物を得た。
[Example 3]
10.0 parts of the alkali-soluble resin C is dissolved in 63.5 parts of butyl lactate, and 1.5 parts of the organic dye derivative C and 25 parts of HOSTAPERM RED E5B 02 (Clariant quinacridone pigment) are added uniformly with a high speed mixer. After stirring and mixing for about 30 minutes, the mixture was dispersed in a 0.6 L horizontal sand mill for 1 hour per 1 kg of the mill base.
Using the obtained dispersion, a pigment composition was obtained in the same manner as in Example 1.
[実施例４]
アルカリ可溶性樹脂Ａ１４．０部をジエチレングリコールモノエチルエーテルアセテート（以下ＥＤＧＡｃという）４９．０部に溶解し、有機色素誘導体Ｄ２．０部およびＨＯＳＴＡＰＥＲＭ ＹＥＬＬＯＷ Ｈ４Ｇ（クラリアント社製 ベンズイミダゾロン顔料）３５部を投入してハイスピードミキサーにて均一になるまで約３０分間撹拌混合した後、０．６Ｌの横型サンドミルにてミルベース１ｋｇあたり１．２時間分散した。
得られた分散体を用い、実施例１と同様にして顔料組成物を得た。
[Example 4]
14.0 parts of alkali-soluble resin A is dissolved in 49.0 parts of diethylene glycol monoethyl ether acetate (hereinafter referred to as EDGAc), and 2.0 parts of organic dye derivative D and 35 parts of HOSTAPERM YELLOW H4G (Clariant benzimidazolone pigment) are added. The mixture was stirred and mixed for about 30 minutes with a high-speed mixer and then dispersed for 1.2 hours per kg of the mill base with a 0.6 L horizontal sand mill.
Using the obtained dispersion, a pigment composition was obtained in the same manner as in Example 1.
[実施例５]
アルカリ可溶性樹脂Ｂ１０．５部をＢＧＡｃ５８．０部に溶解し、有機色素誘導体Ｅ１．５部およびＮＯＶＯＰＥＲＭ ＹＥＬＬＯＷ ４Ｇ（クラリアント社製 ジスアゾ顔料）３０部を投入してハイスピードミキサーにて均一になるまで約３０分間撹拌混合した後、０．６Ｌの横型サンドミルにてミルベース１ｋｇあたり１．２時間分散した。
得られた分散体を用い、実施例１と同様にして顔料組成物を得た。
[Example 5]
10.5 parts of alkali-soluble resin B is dissolved in 58.0 parts of BGAc, and 1.5 parts of an organic dye derivative and 30 parts of NOVOPERM YELLOW 4G (Disazo pigment made by Clariant) are added until approximately uniform with a high-speed mixer. After stirring and mixing for 30 minutes, the mixture was dispersed in a 0.6 L horizontal sand mill for 1.2 hours per 1 kg of the mill base.
Using the obtained dispersion, a pigment composition was obtained in the same manner as in Example 1.
[実施例６]
アルカリ可溶性樹脂Ｃ１５．０部をプロピレングリコールモノモノメチルエーテルアセテート（以下 ＰＧＭＡｃという）２０部とジプロピレングリコールモノメチルエーテル（以下 ＭＰＤＧという）３２．９部の混合溶剤に溶解し、有機色素誘導体Ｃ２．１部およびＣＲＯＭＯＰＨＴＡＬ ＰＩＮＫ ＰＴ（チバスペシャルティーケミカルズ社製 ジメチルキナクリドン顔料）３０部を投入してハイスピードミキサーにて均一になるまで約３０分間撹拌混合した後、０．６Ｌの横型サンドミルにてミルベース１ｋｇあたり１．５時間分散した。
得られた分散体を用い、実施例１と同様にして顔料組成物を得た。
[Example 6]
15.0 parts of alkali-soluble resin C is dissolved in a mixed solvent of 20 parts of propylene glycol monomonomethyl ether acetate (hereinafter referred to as PGMAc) and 32.9 parts of dipropylene glycol monomethyl ether (hereinafter referred to as MPDG), and 2.1 parts of organic dye derivative C And 30 parts of CROMOPHTAL PINK PT (dimethylquinacridone pigment manufactured by Ciba Specialty Chemicals Co., Ltd.), and stirred and mixed with a high speed mixer for about 30 minutes until 1 part per 1 kg of mill base in a 0.6 L horizontal sand mill. Dispersed for 5 hours.
Using the obtained dispersion, a pigment composition was obtained in the same manner as in Example 1.
[実施例７]
アルカリ可溶性樹脂Ａ１５．０部をＭＰＤＧ５２．９部に溶解し、有機色素誘導体Ａ２．１部およびモナーク８００（キャボット社製 カーボンブラック顔料）３０部を投入してハイスピードミキサーにて均一になるまで約３０分間撹拌混合した後、０．６Ｌの横型サンドミルにてミルベース１ｋｇあたり１．５時間分散した。
得られた分散体を用い、実施例１と同様にして顔料組成物を得た。
[Example 7]
15.0 parts of alkali-soluble resin A is dissolved in 52.9 parts of MPDG, and 2.1 parts of organic dye derivative A and 30 parts of Monarch 800 (carbon black pigment manufactured by Cabot Corporation) are added thereto until approximately uniform with a high speed mixer. After stirring and mixing for 30 minutes, the mixture was dispersed in a 0.6 L horizontal sand mill for 1.5 hours per 1 kg of the mill base.
Using the obtained dispersion, a pigment composition was obtained in the same manner as in Example 1.
[実施例８]
実施例７におけるアルカリ可溶性樹脂Ａを、アルカリ可溶性樹脂Ｂに代えて同様の方法にて分散した。
得られた分散体を用い、実施例１と同様にして顔料組成物を得た。
[Example 8]
The alkali-soluble resin A in Example 7 was dispersed by the same method in place of the alkali-soluble resin B.
Using the obtained dispersion, a pigment composition was obtained in the same manner as in Example 1.
[実施例９]
実施例７におけるアルカリ可溶性樹脂Ａをアルカリ可溶性樹脂Ｃに代えて同様の方法にて分散した。
得られた分散体を用い、実施例１と同様にして顔料組成物を得た。
[Example 9]
The alkali-soluble resin A in Example 7 was replaced by the alkali-soluble resin C and dispersed in the same manner.
Using the obtained dispersion, a pigment composition was obtained in the same manner as in Example 1.
[比較例１]
有機色素誘導体Ａを使用しない以外は実施例１と同様の方法にて分散し、顔料組成物を得た。
[Comparative Example 1]
A pigment composition was obtained by dispersing in the same manner as in Example 1 except that the organic dye derivative A was not used.
[比較例２]
実施例１におけるアルカリ可溶性樹脂Ａをアルカリ可溶性樹脂Ｄに変更した以外は同様の方法で分散し、顔料組成物を得た。
[Comparative Example 2]
A pigment composition was obtained by dispersing in the same manner except that the alkali-soluble resin A in Example 1 was changed to the alkali-soluble resin D.
[比較例３]
実施例１におけるアルカリ可溶性樹脂Ａをアルカリ可溶性樹脂Ｅに変更した以外は同様の方法で分散し、顔料組成物を得た。
[Comparative Example 3]
A pigment composition was obtained by dispersing in the same manner except that the alkali-soluble resin A in Example 1 was changed to the alkali-soluble resin E.
[比較例４]
実施例３におけるアルカリ可溶性樹脂ＣをアジスパーＰＢ−８２１（味の素ファインテクノ社製、酸価１７ｍｇＫＯＨ／ｇ）に変更し、さらに、有機色素誘導体を使用しないで同様の方法にて分散し、顔料組成物を得た。
[Comparative Example 4]
The alkali-soluble resin C in Example 3 was changed to Azisper PB-821 (manufactured by Ajinomoto Fine Techno Co., Ltd., acid value 17 mgKOH / g), and further dispersed in the same manner without using an organic dye derivative, and a pigment composition Got.
[比較例５]
実施例４におけるアルカリ可溶性樹脂ＡをＳＰ２４０００（ルーブリゾール社製、酸価０ｍｇＫＯＨ／ｇ）に変更し、さらに、有機色素誘導体を使用しないで同様の方法にて分散し、顔料組成物を得た。
[Comparative Example 5]
The alkali-soluble resin A in Example 4 was changed to SP24000 (manufactured by Lubrizol, acid value 0 mgKOH / g), and further dispersed in the same manner without using an organic dye derivative to obtain a pigment composition.
[比較例６]
実施例５におけるアルカリ可溶性樹脂ＢをＳＰ３２０００（ルーブリゾール社製、酸価０ｍｇＫＯＨ／ｇ）に変更し、同様の方法にて分散し、顔料組成物を得た。
[Comparative Example 6]
The alkali-soluble resin B in Example 5 was changed to SP32000 (manufactured by Lubrizol, acid value 0 mgKOH / g), and dispersed in the same manner to obtain a pigment composition.
[比較例７]
有機色素誘導体Ａを使用しない以外は実施例７と同様の方法にて分散し、顔料組成物を得た。
[Comparative Example 7]
A pigment composition was obtained by dispersing in the same manner as in Example 7 except that the organic dye derivative A was not used.
[比較例８]
実施例７におけるアルカリ可溶性樹脂Ａをアルカリ可溶性樹脂Ｄに変更した以外は同様の方法にて分散し、顔料組成物を得た。
[Comparative Example 8]
A pigment composition was obtained by dispersing in the same manner except that the alkali-soluble resin A in Example 7 was changed to the alkali-soluble resin D.
実施例１〜９および比較例１〜８の顔料分散物について、（１）粘度、（２）分散粒径、（３）分散性、（４）保存安定性、（５）溶剤乾燥後のインキ再溶解性の評価をした。それぞれの測定法を以下に示す。 For the pigment dispersions of Examples 1 to 9 and Comparative Examples 1 to 8, (1) viscosity, (2) dispersed particle size, (3) dispersibility, (4) storage stability, (5) ink after solvent drying Re-solubility was evaluated. Each measurement method is shown below.
（１）粘度：顔料分散物を２５℃に調製し、ビスコメイトＶＭ−１００Ａ（山一電機製、超音波振動式粘度計）にて測定した。 (1) Viscosity: The pigment dispersion was prepared at 25 ° C. and measured with Viscomate VM-100A (manufactured by Yamaichi Denki, ultrasonic vibration viscometer).
（２）分散粒径：顔料分散物を酢酸エチル溶液で２００倍〜１０００倍に希釈し、マイクロトラックＵＰＡ１５０（日機装社製、湿式粒度分布計）にて、体積基準の５０％径を測定した。 (2) Dispersion particle diameter: The pigment dispersion was diluted 200 to 1000 times with an ethyl acetate solution, and a 50% diameter on a volume basis was measured with Microtrac UPA150 (manufactured by Nikkiso Co., Ltd., wet particle size distribution meter).
（３）分散性：上記（１）（２）の測定結果を総合判断し、分散性良好を○、若干良好を△、不良を×とした。 (3) Dispersibility: The measurement results of the above (1) and (2) were comprehensively judged.
（４）保存安定性：顔料分散物をボトル型のガラス容器に入れ、７０℃の恒温機に１週間保存し経時促進させた。保存前後の顔料分散物の粘度を測定した。この時の粘度測定は（１）の粘度測定と同様の方法で実施した。粘度の変化率が±１０％以内なら○、±１０％を越えたら×とした。 (4) Storage stability: The pigment dispersion was placed in a bottle-shaped glass container and stored in a thermostat at 70 ° C. for 1 week to promote the aging. The viscosity of the pigment dispersion before and after storage was measured. The viscosity measurement at this time was carried out by the same method as the viscosity measurement of (1). If the rate of change in viscosity was within ± 10%, it was rated as ○, and if it exceeded ± 10%, it was marked as ×.
（５）溶剤乾燥後の再溶解性：顔料分散物を、バーコーターを用いてガラス板に塗布し、１００℃、２分間乾燥させた。次いで、そのガラス板を酢酸エチル溶液中に浸漬し、溶液の着色を観察した。着色が大きいものを×、若干着色するものを△、ほとんど着色しないものを○と判定した。 (5) Re-solubility after solvent drying: The pigment dispersion was applied to a glass plate using a bar coater and dried at 100 ° C. for 2 minutes. Next, the glass plate was immersed in an ethyl acetate solution, and the coloring of the solution was observed. The case where coloring was large was determined as x, the case where coloring was slightly, Δ, and the case where coloring was hardly performed was determined as ○.
実施例１〜９の顔料分散物は分散性、保存安定性及び溶剤乾燥後の再溶解性に優れていた。特に顔料がカーボンブラックにおいて分散性向上の顕著な効果が認められた。一方、比較例１〜８の顔料分散物は分散性も保存安定性も不良であった。また、溶剤乾燥後の再溶解性も良好でなかった。 The pigment dispersions of Examples 1 to 9 were excellent in dispersibility, storage stability, and re-solubility after solvent drying. In particular, a remarkable effect of improving dispersibility was observed when the pigment was carbon black. On the other hand, the pigment dispersions of Comparative Examples 1 to 8 were poor in dispersibility and storage stability. Moreover, the re-solubility after solvent drying was not good.
本発明の顔料組成物は、印刷インキの用途に限定されるものではなく、カラーフィルター用にも使用することができる。 The pigment composition of the present invention is not limited to the use of printing ink, but can also be used for color filters.
Claims (4)
下記一般式（１）で示される酸性官能基含有有機色素誘導体と、
アミノ基または第４級アンモニウム塩を有するアルカリ可溶性樹脂と、
有機溶剤とを含む顔料組成物であって、
アミノ基または第４級アンモニウム基を有するアルカリ可溶性樹脂の塩基性基当量が３０００〜２００００ｇ／ｅｑであり、酸価が３０〜２００ｍｇＫＯＨ／ｇである顔料組成物であって、アミノ基または第４級アンモニウム塩を有するアルカリ可溶性樹脂が、アミノアルキル基含有不飽和カルボン酸エステルまたはアミノ基の第４級アンモニウム塩を有するエチレン性不飽和単量体と、カルボキシル基を有するエチレン性不飽和単量体との共重合体である顔料組成物。
（Ｐ−Ｘ）-［Ｎ（Ｒ１，Ｒ２，Ｒ３，Ｒ４）］+ 一般式（１）
(式中、Ｐはアゾ系、ベンズイミダソロン系、フタロシアニン系、キナクリドン系、アントラキノン系、ジオキサジン系、ジケトビロロピロール系、キノフタロン系、イソインドリノン系、イソインドリン系、ペリレン系、ペリノン系、ブラバンスロン系、ピランスロン系、及び、アソスラピリミジン系から選ばれる少なくとも一種の有機色素残基を、Ｘはスルホン酸基またはカルボン酸基を、Ｒ１は炭素数５〜２０のアルキル基を、Ｒ２，Ｒ３，Ｒ４はそれぞれ独立に水素原子または炭素数１〜２０のアルキル基を表す。) Pigments,
An acidic functional group-containing organic dye derivative represented by the following general formula (1);
An alkali-soluble resin having an amino group or a quaternary ammonium salt;
A pigment composition comprising an organic solvent,
An alkali-soluble resin having an amino group or a quaternary ammonium group has a basic group equivalent of 3000 to 20000 g / eq and an acid value of 30 to 200 mg KOH / g, wherein the amino group or quaternary An alkali-soluble resin having an ammonium salt is an ethylenically unsaturated monomer having an aminoalkyl group-containing unsaturated carboxylic acid ester or a quaternary ammonium salt of an amino group, and an ethylenically unsaturated monomer having a carboxyl group A pigment composition which is a copolymer of
(PX) - [N (R1, R2, R3, R4)] + General formula (1)
(In the formula, P represents azo, benzimidazolone, phthalocyanine, quinacridone, anthraquinone, dioxazine, diketopyrrolopyrrole, quinophthalone, isoindolinone, isoindoline, perylene, perinone. , At least one organic dye residue selected from Bravanthrone, pyranthrone, and asosurapyrimidine, X is a sulfonic acid group or carboxylic acid group, R1 is an alkyl group having 5 to 20 carbon atoms, R2 , R3 and R4 each independently represents a hydrogen atom or an alkyl group having 1 to 20 carbon atoms.)
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